P
US8956801B2ActiveUtilityPatentIndex 51

Resist composition and method of forming resist pattern

Assignee: TOKYO OHKA KOGYO CO LTDPriority: Feb 17, 2012Filed: Feb 14, 2013Granted: Feb 17, 2015
Est. expiryFeb 17, 2032(~5.6 yrs left)· nominal 20-yr term from priority
Inventors:MATSUZAWA KENSUKE
H10P 76/20C08F 220/28G03F 7/0392G03F 7/0045C08F 220/18H01L 21/0271C07C 69/757G03F 7/20G03F 7/004C08F 220/14C07C 69/54C08F 220/38Y10S430/114C08F 220/282C08F 220/382C08F 220/1818G03F 7/26G03F 7/028G03F 7/2037G03F 7/0382
51
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Cited by
32
References
20
Claims

Abstract

A resist composition including a base component which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, and an organic solvent component, the base component containing a resin component having a structural unit which generates acid, and the organic solvent component containing an organic solvent component including a compound represented by general formula (s-1) shown below in which X represents a single bond or an alkylene group of 1 to 3 carbon atoms; and n represents an integer of 0 to 3.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A resist composition comprising:
 a base component (A) which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, wherein the base component (A) comprises a resin component (A0) comprising a structural unit (a0) which generates acid; and 
 an organic solvent component (S) that comprises an organic solvent component (S1) comprising a compound represented by general formula (s-1) shown below: 
 
       
         
           
           
               
               
           
         
       
       wherein X represents a single bond or an alkylene group of 1 to 3 carbon atoms; and n represents an integer of 0 to 3. 
     
     
       2. The resist composition according to  claim 1 , wherein the structural unit (a0) comprises a group represented by general formula (a0-1) or (a0-2) shown below: 
       
         
           
           
               
               
           
         
       
       wherein Q 1  and Q 2  each independently represents a single bond or a divalent linking group; R 3 , R 4  and R 5  each independently represents an organic group, provided that R 4  and R 5  may be mutually bonded to form a ring with the sulfur atom in the formula; V −  represent a counteranion; A −  represents an organic group containing an anion; and M m+  represents a counter cation; and m represents an integer of 1 to 3. 
     
     
       3. The resist composition according to  claim 1 , wherein the resin component (A0) is a resin component (A1) which exhibits increased polarity by the action of acid. 
     
     
       4. A method of forming a resist pattern, comprising: using a resist composition of  claim 1  to form a resist film on a substrate, subjecting the resist film to exposure, and subjecting the resist film to developing to form a resist pattern. 
     
     
       5. The resist composition according to  claim 1 , wherein X represents a chain-like alkyl group of 1 to 3 carbon atoms. 
     
     
       6. The resist composition according to  claim 1 , wherein n represents 1 or 2. 
     
     
       7. The resist composition according to  claim 1 , wherein the organic solvent component (S1) comprises a compound represented by any one of formulae (s1-1-1) to (s1-1-8) shown below: 
       
         
           
           
               
               
           
         
       
     
     
       8. The resist composition according to  claim 1 , wherein the organic solvent component (S1) is a tetrahydrofurylalcohol. 
     
     
       9. The resist composition according to  claim 1 , wherein the structural unit (a0) comprises a structural unit represented by general formula (a0-11′) or (a0-21′) shown below: 
       
         
           
           
               
               
           
         
       
       wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Q 1  and Q 2  each independently represents a single bond or a divalent linking group; R 3 , R 4  and R 5  each independently represents an organic group, provided that R 4  and R 5  may be mutually bonded to form a ring with the sulfur atom in the formula; V −  represent a counteranion; L 1  represents —O—, —C(═O)—O—, —C(═O)—NH— or a single bond; R y1  represents a single bond or a divalent hydrocarbon group which may have a substituent; A − represents an organic group containing an anion; and M m+  represents a counter cation; and m represents an integer of 1 to 3. 
     
     
       10. The resist composition according to  claim 1 , wherein the resin component (A0) further comprises a structural unit (a2 s ) derived from an acrylate ester containing a —SO 2 — containing cyclic group, provided that the structural unit (a0) is excluded from the structural unit (a2 s ). 
     
     
       11. The resist composition according to  claim 10 , wherein the structural unit (a2 s ) is represented by general formula (a2-0) shown below: 
       
         
           
           
               
               
           
         
       
       wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; R 28  represents a —SO 2 — containing cyclic group; and R 29  represents a single bond or a divalent linking group. 
     
     
       12. The resist composition according to  claim 10 , wherein the structural unit (a2 s ) is represented by general formula (a2-0-1) shown below: 
       
         
           
           
               
               
           
         
       
       wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; R 28  represents a —SO 2 — containing cyclic group; and R 30  represents a divalent linking group. 
     
     
       13. The resist composition according to  claim 11 , wherein R 28  represents a group represented by any one of formulae (3-1) to (3-4) shown below: 
       
         
           
           
               
               
           
         
       
       wherein A′ represents an oxygen atom, a sulfur atom or an alkylene group of 1 to 5 carbon atoms which may contain an oxygen atom or a sulfur atom; z represents an integer of 0 to 2; and R 27  represents an alkyl group, an alkoxy group, a halogenated alkyl group, a hydroxyl group, —COOR″, —OC(═O)R″, a hydroxyalkyl group or a cyano group, wherein R″ represents a hydrogen atom or an alkyl group. 
     
     
       14. The resist composition according to  claim 12 , wherein R 28  represents a group represented by any one of formulae (3-1) to (3-4) shown below: 
       
         
           
           
               
               
           
         
       
       wherein A′ represents an oxygen atom, a sulfur atom or an alkylene group of 1 to 5 carbon atoms which may contain an oxygen atom or a sulfur atom; z represents an integer of 0 to 2; and R 27  represents an alkyl group, an alkoxy group, a halogenated alkyl group, a hydroxyl group, —COOR″, —OC(═O)R″, a hydroxyalkyl group or a cyano group, wherein R″ represents a hydrogen atom or an alkyl group. 
     
     
       15. The resist composition according to  claim 10 , wherein the resin component (A0) further comprises a structural unit (a1) containing an acid decomposable group that exhibits increased polarity by the action of acid, provided that the structural unit (a1) is excluded from the structural unit (a2 s ). 
     
     
       16. The resist composition according to  claim 15 , wherein the structural unit (a1) is represented by general formula (a11-0-12) shown below: 
       
         
           
           
               
               
           
         
       
       wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; R 23  represents a branched alkyl group; R 24  represents a group which forms an aliphatic polycyclic group with the carbon atom to which R 24  is bonded. 
     
     
       17. The resist composition according to  claim 7 , wherein
 the structural unit (a0) comprises a structural unit represented by general formula (a0-11′) or (a0-21′) shown below, and 
 the resin component (A0) further comprises a structural unit (a2 s ) derived from an acrylate ester containing a —SO 2 — containing cyclic group, provided that the structural unit (a0) is excluded from the structural unit (a2 s ): 
 
       
         
           
           
               
               
           
         
       
       wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Q 1  and Q 2  each independently represents a single bond or a divalent linking group; R 3 , R 4  and R 5  each independently represents an organic group, provided that R 4  and R 5  may be mutually bonded to form a ring with the sulfur atom in the formula; V −  represent a counteranion; L  1  represents —O—, —C(═O)—O—, —C(═O)—NH— or a single bond; R y1  represents a single bond or a divalent hydrocarbon group which may have a substituent; A −  represents an organic group containing an anion; and M m+  represents a counter cation; and m represents an integer of 1 to 3. 
     
     
       18. The resist composition according to  claim 17 , wherein the resin component (A0) further comprises a structural unit (a1) represented by general formula (a11-0-12) shown below: 
       
         
           
           
               
               
           
         
       
       wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; R 23  represents a branched alkyl group; R 24  represents a group which forms an aliphatic polycyclic group with the carbon atom to which R 24  is bonded. 
     
     
       19. The resist composition according to  claim 8 , wherein
 the structural unit (a0) comprises a structural unit represented by general formula (a0-11′) or (a0-21′) shown below, and 
 the resin component (A0) further comprises a structural unit (a2 s ) derived from an acrylate ester containing a —SO 2 — containing cyclic group, provided that the structural unit (a0) is excluded from the structural unit (a2 s ): 
 
       
         
           
           
               
               
           
         
       
       wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Q 1  and Q 2  each independently represents a single bond or a divalent linking group; R 3 , R 4  and R 5  each independently represents an organic group, provided that R 4  and R 5  may be mutually bonded to form a ring with the sulfur atom in the formula; V −  represent a counteranion; L 1  represents —O—, —C(═O)—O—, —C(═O)—NH— or a single bond; R y1  represents a single bond or a divalent hydrocarbon group which may have a substituent; A −  represents an organic group containing an anion; and M m+  represents a counter cation; and m represents an integer of 1 to 3. 
     
     
       20. The resist composition according to  claim 19 , wherein the resin component (A0) further comprises a structural unit (a1) represented by general formula (a11-0-12) shown below: 
       
         
           
           
               
               
           
         
       
       wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; R 23  represents a branched alkyl group; R 24  represents a group which forms an aliphatic polycyclic group with the carbon atom to which R 24  is bonded.

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